


Winchester's and an Angel

by AlexTheShipper



Category: Supernatural
Genre: AU mafia, Assasin Gabriel, Assassin Anna, Don Dean, Ex prostitute Anna, Friends to Lovers, Lucifer's an asshole, M/M, Slow Burn, fighting brothers, mentioned rape/non-con not explicit, past trauma
Language: English
Status: In-Progress
Published: 2014-10-30
Updated: 2014-11-16
Packaged: 2018-02-23 06:46:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 2,608
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2538155
Author URL: https://archiveofourown.org/users/AlexTheShipper/pseuds/AlexTheShipper
Summary: <blockquote class="userstuff">
              <p>The Angeles family recently lost a large portion of it's family when Lucifer broke away from the family and started stealing their land. Financial situations and paranoia lead Michael to sell his brother to the neighboring Winchester family.</p>
            </blockquote>





	1. The break up of the Angeles family

Lucifer lounged in a large white chair, his red suit the only spot of color in the pristine white room. The walls were a soft cream, the carpet a bleached white, and the furniture was either steel or white. Castiel observed the contrast of his brother and the room from where he sat on the couch. The sound of a door opening caused him to look away smiling at his eldest brother, who took no notice. He didn’t know it, but this was the beginning of the end.

“Lucifer, what is this?” Michael held a paper out voice cold and angry.

“Well, Michael, it looks like a sheet of paper. I’m right aren’t I?” Lucifer looked up from his laptop with a sarcastic smile. Castiel sat on the pristine white couch trying to look small while his brothers argued.

“Yes.” Lucifer smirks at him. “It is a sheet of paper and this sheet of paper says you’re making under the table deals without my knowledge.” Michael was tense as he waved the paper towards his brother.

“Yes Michael I am. You aren’t Chuck.” Lucifer stood up glaring at his brother. “Ever since Chuck fucked off to write his damn book you act like you’re in charge.”

“I am in charge, I’m the oldest.” Lucifer laughed thinking he sounded like a child.

“Perhaps, but only by four minutes. I will do as I please brother.” Lucifer left the room.

“Michael?” Castiel looked up nervously.

“Yes Castiel?” His big brother tapped his foot impatiently.

“I was simply wondering why you and him keep fighting.” Castiel looks up hoping it’s something that can be fixed.

“Don’t worry about it brother, I will handle it.” Castiel nodded and picked up his book turning his attention back to it.

“I’m just worried about Luce is all.” Castiel whispered not realizing the mistake he had made in letting Michael hear him.

…

“I’m leaving Michael. Good luck keeping your territory.” Lucifer stormed out Anna close behind. He’d built up a number of loyal followers within the Angeles organization before leaving and with Lillith and Anna at his side he left his old life behind. He had his own organization now. Crowley worked finances and Azazeal, and Allistair made up the brute force. He called his organization prodigy and with a number of drug dealers he started taking over Michael’s territory.

“Well are you going to follow him?” Michael glared at Castiel a paranoid glint in his eyes while Zacheria eyed him coldly.

“Of course not brother.” Castiel was 18 now and he smiled innocently at his brother. “I do not wish to leave you.” Despite the reassuring words it was clear Michael didn’t trust him. Castiel was kept away from the books after that despite his affinity for understanding any given situation Michael kept him away from the business altogether. Zacheria was given the jobs of keeping the books, his focus on gaining power led to a considerable oversight and Michael found himself deeply indebted to the Winchesters.

…

“Yes, I’m aware.” Michael sat rigidly as he spoke into the phone. “I just don’t have the money, if you give us more time-” Michael flipped through the book in front of him. “Yes that could work. My brother, Castiel you say?” Castiel tensed beside him, waiting for his brother to finish. “Five on Sunday at the reservoir, got it thank you.” He snapped the phone shut.

“What about me Michael?” Castiel stood to follow his brother as he left.

“You’re going to the Winchester’s they’ll probably whore you out to help pay for my debt. I don’t know. Go pack a bag.” Gabriel stood stunned in the hallway.

“Did I hear that right?” Gabriel gaped after their brother as Castiel nodded numbly. He went to do what was asked.

“I’m afraid so Gabriel.” Castiel sighed softly and pulled Gabriel into his room. “Help me pack?” Gabriel looked around the light blue room. He wasn’t sure what there was to pack other than the small picture of their mother that covered a family photo with all of the brothers.

“I don’t think you need help. I need to go pack my own things.” Gabriel turned to leave.

“What did he sell you too?” Castiel hissed bitterly.

“No, the idiot sold my little brother and now he has a well-trained assassin ready to kill him. I’m coming with you I just need to make a call.” Gabriel left with that remark and Castiel heard him greet a ‘Sam’ on the phone. He put the photo in the bottom of his suit case and began packing his suit case hands lingering on the coat his father had left him. He pulled it on over his suit his Angeles blade in the pocket.

…

“You did it Sam.” Gabriel smiled as he packed his bags.

“Of course I did. You asked me to.” Gabriel blushed tossing in his boxers along with a supply of rifles and other weapons. “It wasn’t hard though. I can’t imagine living with that bastard. John was a shit parent but even he wasn’t that cold. All I did was ask Gabriel.” Gabriel hummed into the phone as he finished packing.

“I know Sammy, he sucks. We’re getting out now though thanks to you.” Gabriel smiles at himself.

“Your brother really doesn’t mind right?” Gabriel listens to Sam’s beautiful laugh with a smile.

“Of course not. Dean’s always happy to help.”


	2. Sister Dearest

Gabriel slipped out of the house with his bags at around noon a note propped up on his bed as explanation.

_If you’re selling family members I’m not sticking around until you decide to sell me too. You’re lucky I’m not going to kill you._

_The Trickster_

…

Michael read the note with a stoic expression.

“Uriel.” The large police officer appeared beside him.

“Yes sir.” The man was a cousin of Michaels and had thus far remained loyal.

“Please make sure nobody bothers us at the Reservoir tonight.” Michael didn’t wait for an answer as he walked away.

…

“Hey Gabe.” Sam smiled as he opened the door.

“Hey Sammy.” The giant leans in to hug him as Dean yells from the kitchen.

“I thought only I got to call you Sammy!” Gabriel stuck his tongue out at him.

“Dean, you know I don’t like you calling me Sammy.” Sam called back.

“Then why can he do it?” Dean pouted walking into the room.

“Well one he’s cuter and two it’s better than Samsquatch.” Gabriel pretends to feel insulted.

“Samsquatch you wound me. That is the perfect nickname for you with your moose-like size.” Sam looked affronted.

“Yeah well you’re… tiny.” Sam blushed when Dean laughed at him long hair falling into his eyes.

“Yeah wonderful insult Sam. Anyways we need to talk about the meet tonight.” Everyone settled onto the comfortable couches the mood immediately more serious. “Castiel had quite the shake down this afternoon. Michael basically told him he was gonna be used as a whore to pay for the debt.” Dean growled softly.

“I wanna pop that asshole so bad.” Dean pulled out his phone, it was nearing one and preparations needed to be made for tonight.

“Dean you know we can’t risk a fight with them.” Dean sighs.

“I know Sam doesn’t mean I have to like it. Bobby! Get in here!” The old man ambled in shooting a glare Dean’s way.

“What do you want idjit?” Gabriel stifled his laughter at this old guy calling a Don, an idjit.

“We got a drop at the reservoir tonight, I need a crew.” Dean raised an eyebrow at Gabriel’s laughter glancing at Sam for an explanation.

“Jo?” Dean nodded “You want Kate cleared from the area?” Again a kurt nod.

“Put Rufus on a roof somewhere, and make sure Benny is available I need some muscle. Samsquatch you’re staying here.” Sam looked ready to protest. “No Sam. Michael is not someone I trust, if I’m going you aren’t. Don’t worry I’ll be armed to the teeth.” Gabriel looks ready to burst. “Gabe?”

“Do you know where my sister Anna is? Her and Cas used to be really close.” Sam gaped at him.

“Anna is your sister?” Dean was the first to find his voice. “I’ll be right back.” He left the room listening to muffled conversation behind him as he exited the building, headed for the spare housing out back.

…

“Anna.” She looked up at him clearly nervous and he sat down attempting to look non-threatening. “Your brother is here.” She scrambled back.

“Keep Luce the fuck away.” She growled at him.

“I mean Gabriel, your brother Castiel is coming to stay with us as well.” She chews her lip.

“Cassie? He’s okay?” Dean shrugged.

“Probably just terrified his brother sold him.” She whistled softly. “He could probably use a familiar face will you come and wait in the car?” Dean smiled at her happily.

“Yes that would be fine.” She smiles and stands up keeping a careful distance between them.

“Let’s go see your tiny brother than shall we.” Dean smirks at her.

“I’m younger you know.” She pointed out with a smile.

“Funny, so is Sammy. What’s with you giant younger siblings?” She laughed as he led her back to the living room.

The room was silent when they entered and Gabriel stared frozen at Anna. Dean gestured for her to sit down before settling next to Sam.

“Hi Gabriel.” Her voice was careful and calculating in a way that none of them had heard before.

 “Anna? You’re really here?” Gabriel moved toward her and she shifted toward the exit automatically.

“Yes. Hey guys, you mind clearing out. Send Benny in though. He’s calming.” Sam was the first to move grabbing Dean by the arm and dragging him out of the room. Anna waits for Benny to enter before turning back to her brother. “Yes Gabe I’m here.” Benny noted the tension and settled between them with ease.

“Bro, just so you know I’m a trained assassin you’re probably couldn’t stop me if I decided to pull shit.” Benny looked at him with a cold smile.

“Brother, it’s not my job to take you down. She’s the one currently carrying three guns and five knives?” He glanced over questioningly.

“Six knives Benny. You forgot the vampirate one you gave me. The red and blue jewels on the handle are pretty don’t you think Gabriel?” She pulled the knife out with barely a flick of her wrist. Gabriel managed to cover his surprise with an impressed nod. It truly was impressive a single blood red ruby on the handle surrounded by a variety of blues and greens.

“Okay now that we’re done comparing dick sizes or in this particular case knife sizes, what happened to you? I haven’t seen you since Lucy left.” She flinches at the mention of his name the knife twirling in her hand.

“Lucifer is an asshole. He treated me like shit. I escaped his stupid brothel, hell’s bells, Benny here found me and the Winchester’s took me in.” Gabriel hand twitched for his gun, he wanted to shoot his brothers. The twins had taken this too far. “I’m not the only one. Meg used to work for him too.” Gabriel looked ready to ask a question, but she cut him off. “That’s all you need to know. Now I’m gonna go pick up my brother from your idiot twin, and you’re going to stay here and refrain from pranking me.” She leaves shortly after that Benny on her heels. Gabriel numbly finds himself wandering off in search of Sam.

**Notes for the Chapter:**

> Family line up as of now
> 
> Angeles   
> (Same as previous without Gabriel)
> 
> Winchester's   
> Sam  
> Dean  
> Benny   
> Anna  
> Meg
> 
> Demon's   
> Same with out Anna


	3. Traded

“Castiel, it’s time to go.” Michael yelled from the doorway and Castiel dragged his suitcase to the door. Castiel tied his tie with shaking hands before grabbing his bag in an attempt to remove his jacket. Michael walked in and with a snap his bag jacket still inside was taken from him to be put in the car.

"Your phone and lap top will not be going with you, I cannot risk you sharing sensitive information." Castiel doesn't bother to defend himself.

"Thank you for carrying my bag Uriel." The other man only grunts at him and Castiel trails after Michael as Zacheria babbles about the finances of this trade.

 

They stepped outside into the cold air and Castiel was forced to suppress a shiver. There would be no point arguing, he was being sold and there wasn't anything that would convince Michael otherwise.

The car ride was mostly silent. Michael speaking on the phone as Castiel stares out the window. If he had his iPod he'd be listening to music instead of silently mourning his freedom.

The car pulls to a halt and Michael climbs out barely waiting for him before barking orders to the guards. With two dons present there's a lot of fire power out. Gadreel and Tessa are both armed to the teeth and Castiel's sure someone is on a roof nearby. Everyone aside from him is bundled in warm coats and gloves and its mere moments before he's shivering.

"Michael." Everyone turns toward the voice Castiel trying to calm his trembling as he eyes his new don. The man is extremely attractive and his green eyes flash intimidatingly as he glances at Michael. The meaning will be lost on his brother but Castiel has to try and suppress another shiver at the cold disdain in his eyes.

"Dean it's so nice to see you again." Michael offers a fake smile and Dean nods absently gesturing something to the man beside him.

"You as well Michael. Is that Castiel?" Dean pointed to him with a smile.

"Yes, Castiel go say hello." Castiel froze, staring pleadingly at Michael. “Go.” There was no room for argument and Michael shoved him forward.

“Hello, Dean.” Castiel fidgeted nervously and suddenly the man Dean had sent off returns with an old leather jacket.

“Hey, Cas. You cold?” Dean takes the jacket and hands it to him.

“Yes, thank you.” The Jacket is warm and smells strangely of motor oil. Castiel finds it comforting and he waits nervously, silent beside Dean as they iron out the details. It’s clear there will be no rescue or regret from Michael, instead he waits for Gabriel. Gabriel had always protected him. Everything seemed to be winding down and Dean led Cas to the car. The door opened to reveal a familiar head of red hair and Castiel panicked.

“Why is Anna here? Where is Lucifer? Please.” He trembled and suddenly strong hands helped him into the car.

“Anna is here of her own free will, Lucifer is currently…” He shot Benny a questioning look.

 “Lucifer is at his club hell’s bell’s according to our intel.” Anna had noticeably stiffened and Benny glared at Dean. “My apologies Anna.”

“It’s okay Benny.” Castiel looked increasingly confused as they spoke. “Dean, can we leave?” With a small nod, and a few words from Benny the car was moving and Anna once again told her story. Castiel was left shell shocked by the story of Lucifer’s treatment of his sister. “The Winchester’s here took me in after Benny got me out. They let me stay on their property and I'm head assassin despite Gabriel's appearance." Castiel managed to hid his surprise and she continued speaking. "I also help with the drug’s side of business with Benny as my personal body guard best friend and head dealer.” The news that the Winchester’s had helped his sister was calming but she had come of her own free will and he had been sold. He was property to them and he wasn’t yet sure he would be afforded the same courtesies.

**Author's Note:**

> Current known line up for the families 
> 
> Winchester  
> Sam   
> Dean
> 
> Angeles  
> Michael  
> Zacheria   
> Gabriel   
> Castiel
> 
> Demons  
> Lucifer  
> Lillith  
> Anna  
> Alistair   
> Crowley   
> Azazeal


End file.
